Ashland Homes for Sale

Welcome to Ashland, a picturesque gem nestled in the heart of Southern Oregon! Known for its vibrant arts scene, stunning natural beauty, and a strong sense of community, Ashland offers an idyllic lifestyle for those seeking a blend of culture and outdoor adventure. With the majestic Cascade Mountains as your backdrop and the serene waters of the Rogue River nearby, outdoor enthusiasts can enjoy hiking, biking, and rafting year-round.

Ashland is perhaps best known for the Oregon Shakespeare Festival, which attracts theater lovers from all over the world. This charming city is also home to delightful boutiques, gourmet restaurants, and local wineries, making it a haven for foodies and art aficionados alike. The friendly atmosphere and welcoming community make Ashland not just a place to live, but a place to thrive.

When it comes to homes for sale, Ashland boasts a diverse range of properties to suit every lifestyle and budget. From cozy bungalows adorned with character to modern family homes with spacious layouts, there’s something for everyone. Many properties feature stunning views of the surrounding mountains or are conveniently located near the vibrant downtown area, allowing residents to enjoy the best of both worlds.

Imagine waking up in a charming home, sipping your morning coffee while taking in the breathtaking landscape, or strolling through the lively streets filled with art and culture. Ashland is not just a destination; it’s a community where dreams can flourish. Explore our listings today and find your perfect home in this enchanting city!

Newest Ashland Homes for Sale

$397,000

3 Beds ⋅ 2 Baths ⋅ 5106400 MLS

Welcome to this pristine 2022 manufactured home, beautifully nestled on a private 1.81 acre lot with picturesque hillside views. Perfect vacation home or investment property! Designed for comfortable, easy living, the home features a bright, inviting open concept layout with luxury vinyl plank flooring throughout the main living areas. The spacious living and dining rooms flow seamlessly into a well appointed kitchen, complete with a large center island, abundant cabinetry and countertop space and stainless steel appliances, perfect for everyday living and entertaining. The primary bedroom offers a private 3/4 bath, while two additional bedrooms and a full bathroom provide plenty of space for family and guests. A dedicated laundry room adds convenience and functionality. Step outside to enjoy the covered porch, ideal for morning coffee, or gather around the firepit area in the evening. The back deck is ready for summer barbeques, while the scenic viewing platform provides the perfect spot to take in the surrounding landscape. Conveniently located just minutes from the Ashland Village center, close to shops, restaurants, Squam Lake, golf, skiing, and countless other Lakes Region attractions. This exceptional property offers the perfect blend of privacy, comfort, and access to all that the area has to offer.

48 Harold Avery Rd, Ashland

$160,000

3 Beds ⋅ 1 Baths ⋅ 5105891 MLS

Opportunity awaits at 25 Mill Street in Ashland! Offered at $160,000, this 3-bedroom, 1-bath home was in the midst of an extensive renovation when circumstances brought the project to an unexpected stop. Much of the interior has already been taken down to the studs, providing the next owner with a head start and a blank canvas to bring their vision to life. Some building materials, including sheetrock and flooring, will remain with the property. The home features a newer metal roof, and a full stone foundation with a dirt floor. A paved driveway leads to a storage shed. Situated on a manageable .14-acre in-town lot with municipal water and sewer, the location offers convenient access to local schools, I-93, Plymouth, Squam Lake, skiing, and all that the Lakes Region has to offer. This property is being sold as-is and will require substantial renovation. Bring your ideas and finish what was started at 25 Mill Street!

25 Mill St, Ashland

$774,900

3 Beds ⋅ 3 Baths ⋅ 73565685 MLS

7 Cedar St, Ashland

$2,149,000

6 Beds ⋅ 5 Baths ⋅ 73564757 MLS

Quietly tucked away at the cul-de-sac’s end, this grand Ashland residence delivers over 5,300 square feet of architectural grandeur and elevated living. Completely remodeled with bespoke updates throughout. The entrance commands attention with its dramatic quartz staircase framed by glass railings, high ceilings, and tailored interior millwork. Sun-soaked open interiors seamlessly flow into a state-of-the-art kitchen and open living areas. This beautiful and elevated luxurious home offers multi-level grand living with six bedrooms, four-and-a-half pristine baths with an adaptable lower level guest suite suited for relatives, guests or dedicated staff. A lavish primary suite boasts spa-grade quartz finishes, heated porcelain floors, custom stone, a soaking tub, and dual vanities. Below, find a fully finished entertainers dream space with Bose surround system inside and dozens of speakers outside on the pool deck. The amazing walkout lower level is warmed by radiant-heated porcelain tile where your private resort unfolds with an in-ground pool, serene Koi pond and a custom mini-golf course for high end entertainment in complete seclusion- the ultimate blend of sophistication, comfort, and lifestyle. Ashland luxury living at it finest. Schedule your private tour of this rare and luxurious Ashland residence before it's gone.

24 Old Connecticut Path, Ashland

$979,900

5 Beds ⋅ 4 Baths ⋅ 73563321 MLS

This inviting 5-bedroom, 3.5-bath colonial home is set on a generous, 3/4 lot, near the top of the hill. The sun-filled main level features a bright family room centered around a cozy wood-burning fireplace. The formal dining room flows into the kitchen with slider to a large deck, perfect for outdoor dining, entertaining, or relaxing. The main suite features 2 closets, ceiling fan, & a full bath. The 3 other bedrooms on this level are generous in size, and provide w/w carpeting. The lower level offers valuable additional living space with a kitchenette, bedroom, full bath, living area, and an office, ideal for in-law, au-pair, or over night guests ! The lower level has direct access to the rear yard. Heating system only 2yo. There is a large driveway leading to the 2 car attached garage. Underground utilities on the street. Walk to Mill Pond Park ! Thoughtfully designed for comfortable everyday living and effortless entertaining. New High Efficient Gas Heating System installed 12/24. Includes Security System w/ 2 cameras and Water Purification system under the Kitchen sink. .Close to Rt. 9, Mass. Pike, 495 etc.

73 Sudbury, Ashland

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 73563084 MLS

Your private retreat awaits on Indian Brook Road. This custom-built 4 bed, 3.5 bath Colonial was designed for both everyday living and effortless entertaining, with an impressive array of amenities and resort-style outdoor space. At the heart of the home is the spacious family room, featuring a wood-burning fireplace, built-in shelving with a window seat and dramatic floor-to-ceiling windows that fill the space with natural light. The room flows seamlessly into the inviting eat-in kitchen with Thermador appliances and new LG refrigerator. The elegant dining room features a tray ceiling accented by sophisticated cove lighting, creating the perfect setting for gatherings and special occasions. The first floor offers exceptional flexibility; the private home office with a closet is located next to a full bath with a step-in shower. This versatile space could easily serve as a main level bedroom depending on your needs. Upstairs you will find the impressive primary suite, complete with a newly remodeled bathroom with soaking tub, two large walk-in closets and a spacious sitting area that provides a private sanctuary for quiet reflection with a beautiful view of the yard. Three generously sized guest bedrooms and a full guest bath round out the second floor. The finished basement provides even more living space and endless possibilities—perfect for a home gym, theater room, or playroom. Located on just under an acre of land, this home is set back from the road which allows for maximum privacy. The large composite back deck overlooks the serene in-ground saltwater pool. The dedicated pool house has a half bath, fridge, sink, outdoor shower and ample storage which makes summer entertaining exceptionally convenient. A private basketball sports court adds another dimension of recreation for family and guests. For nature lovers, the backyard offers something truly special: a trail that brings you to a wooden bridge over beautiful Indian Brook that allows you to hike directly to Hopkinton State Park. An attached two-car garage provides everyday convenience and additional storage.With generous living spaces, flexible accommodations, resort-style outdoor amenities, and direct access to nature, this property offers a rare opportunity to enjoy space, privacy, and comfort all in one exceptional home. A commuter's dream: located close to both the Southborough and Ashland MBTA stations. Easy access to Rt 9 and the Mass Pike.

49 Indian Brook Road, Ashland

$615,000

3 Beds ⋅ 2 Baths ⋅ 73562935 MLS

Offer Deadline Sunday 8/16, 5:00pm!!! Located in one of Ashland's most sought-after neighborhoods, this adorable cape is a short walk to nearby Mill Pond, the local brewery, library, farmer's market, or one of many downtown restaurants. Enjoy the large, private fenced-in backyard with storage shed, mature shade trees and patio...perfect for BBQ's and entertaining, with plenty of room to garden, play, or relax. The large kitchen is nicely laid out with plenty of cabinet space. Formal dining room, 2 full baths, 1 bedroom on the 1st floor (currently staged as a home-office) with 2 additional bedrooms on the 2nd floor. Gleaming hardwoods throughout. The partial finished basement space could be used as a home gym or rec room. The unfinished space would make a great workshop or storage area. Enjoy all that Ashland has to offer, with close proximity to the train, schools, shopping, hiking/biking trails.

51 Pine Hill Rd, Ashland

$450,000

5 Beds ⋅ 2 Baths ⋅ 5104533 MLS

Welcome to 47 Highland Street, a distinctive turn-of-the-century New Englander offering character, space, and flexibility in the heart of Ashland. With approximately 2,600 square feet of living space, this property presents an exciting opportunity for an owner-occupant, investor, or buyer looking for a property with multiple possibilities. Potential to configure the home as two units: one 2-bedroom, 1-bathroom unit, and one 3 bedroom, 1 bath unit. The property also features a three-story barn, offering additional space and the possibility to explore further uses or expansion, subject to approvals. The barn has been updated and includes a charging station for an electric vehicle. Set on approximately 0.43 acres, the property features a mostly level city lot, paved driveway, attached one-car garage with direct entry and storage above. The yard borders the backside of Ashland Elementary, creating a convenient in-town setting.There is even an electric vehicle charger at barn. Inside, the home offers a mix of classic character and practical updates, including split heating and cooling units throughout, radiator-style wall heaters in the bathrooms, and many updates throughout the property. The sunroom has been updated with new windows, adding comfort and natural light to this inviting space. Public water and sewer, high-speed internet availability, and a convenient Ashland location make this property both comfortable and practical. Located just off Route 3, 47 Highland Street is close to the conveniences of downtown Ashland while offering easy access to the Lakes Region and the surrounding White Mountains. The town beach on Little Squam Lake is just a 5 minute drive. Whether you're looking for an income-producing property, a home with room to grow, or a unique New England property to make your own, 47 Highland Street offers character, flexibility, and opportunity.

47 Highland St, Ashland

$350,000

1 Beds ⋅ 1 Baths ⋅ 73561286 MLS

Beautiful flat 1/4-acre lot in a highly desirable Ashland location, just moments from Ashland and Hopkinton State Parks, shopping, dining, and major conveniences. A fantastic opportunity for builders or buyers seeking a prime setting for new construction. Existing small house must be torn down, and the buyer will need to connect to town sewer as the current dwelling is on septic. Contents of the home will remain. Do not enter the structure—land can be walked and explored freely. Create your dream home in one of Ashland’s most sought-after areas.

42 Olive St, Ashland

$399,000

3 Beds ⋅ 1 Baths ⋅ 5102969 MLS

Rare Opportunity – Two Properties Being Sold Together! Unlock the potential of this unique offering at 6 & 8 Field Drive, Ashland, NH. This package includes a 3.8-acre buildable lot at 6 Field Drive and the neighboring 720 sq. ft., 3-bedroom home at 8 Field Drive, creating an exceptional opportunity for builders, investors, or those looking to create their dream property. A standout feature is that 6 Field Drive surrounds 8 Field Drive, allowing the parcels to be combined into one expansive 4.8-acre property (subject to any necessary municipal approvals). With two access points from the main road, the land offers flexibility for future development while the existing home provides immediate use as a seasonal retreat, rental, or temporary residence during construction. Perfectly situated in the heart of New Hampshire's Lakes and White Mountains Region, this property is just minutes from skiing, hiking, snowmobiling, boating, and all the year-round recreation the area is known for. Whether you're envisioning a private mountain getaway, a custom dream home, or simply investing in a highly desirable location, opportunities like this are hard to find. Bring your vision and take advantage of this rare chance to own nearly 5 contiguous acres in one of New Hampshire's premier outdoor destinations.

6-8 Field Dr, Ashland

$675,000

3 Beds ⋅ 3 Baths ⋅ 73557329 MLS

Discover this beautiful like-new Colonial in a prime walk to train location! This sun splashed home offers a flexible and inviting floor plan, featuring a spacious living room that opens seamlessly to the dining room, plus a bright sunroom ideal as a home office or cozy retreat. The beautifully updated kitchen showcases classic white cabinetry, stainless steel appliances, butcher block counters, and a convenient breakfast bar. A first floor half bath with laundry adds everyday ease. High ceilings, gleaming hardwood floors, and a mudroom entry with built in bench elevate the home’s charm and functionality. The private primary suite includes a new bath with double vanities and three closets, including a walk in. Nearly every major feature was updated in 2021—roof, windows, siding, floors, kitchen, and baths—offering peace of mind and modern comfort. Plus it even comes with a whole house generator! The gas heat, town water and sewer, and over 1,700 square feet of above grade living space make this home an exceptional value. Step outside to a covered deck overlooking a beautiful, private backyard framed by woods—your own serene oasis perfect for unwinding, entertaining, or enjoying nature. All of this in an unbeatable commuter location just steps from the Ashland MBTA station and close to downtown. Enjoy easy access to Routes 495, Mass Pike, and Route 9. Ashland offers highly regarded schools, fantastic restaurants and shops, and a spectacular state park filled with scenic trails and outdoor recreation. Come see!

329 Pleasant Street, Ashland

$1,495,000

4 Beds ⋅ 2 Baths ⋅ 5102628 MLS

Nestled along the shores of beautiful Little Squam Lake, this quintessential seasonal waterfront cottage has been cherished by the same family for more than 80 years. Originally built in 1915, the property captures the timeless charm and character of a classic New Hampshire summer retreat. The cottage features an expansive open living and dining area with a brick fireplace, creating the perfect gathering place for family and friends. A staircase with a natural birch handrail leads to the second floor, where you'll find four bedrooms and a 3/4 bath, adding to the home's vintage appeal. The spacious kitchen provides ample room for preparing summer meals and entertaining. Double doors from the living area open onto a lakeside deck. Expansive windows frame picturesque views down the length of the lake, offering breathtaking sunrises and an ever-changing waterfront panorama. A separate seasonal sleeping cottage provides additional accommodations for guests while preserving everyone's privacy. Modern conveniences, including town water and town sewer, complement the property's historic character. Ideally located just minutes from local restaurants, shopping, marinas, hiking trails, and many of the Lakes Region's most popular attractions, this unique offering combines the tranquility of lakeside living with the convenience of nearby amenities. Whether you're continuing a family tradition or creating new memories, this classic lake cottage offers a rare opportunity to own a piece of waterfront history on one of New Hampshire's most sought-after lakes.

51 Leavitt Hill Rd, Ashland

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